Triethylamine → HCID 10150518, compound

HRID 2306624Notes

Reaction equation

HRID 2306624 reaction equation
[C:1](SCC)(=[S:3])[CH3:2].[NH2:7][CH2:8][C@@H:9]1[O:13][C:12](=[O:14])[N:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[S:22][CH2:23][C:24](=[O:27])[NH:25][N:26]=3)=[C:17]([F:28])[CH:16]=2)[CH2:10]1.C(N(CC)CC)C>CN(C=O)C>[F:28][C:17]1[CH:16]=[C:15]([N:11]2[CH2:10][C@H:9]([CH2:8][NH:7][C:1](=[S:3])[CH3:2])[O:13][C:12]2=[O:14])[CH:20]=[CH:19][C:18]=1[C:21]1[S:22][CH2:23][C:24](=[O:27])[NH:25][N:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70093Ethyl dithioacetateHCID 23528997HCID 23528997, compound

Product 1

HCID 10150518HCID 10150518, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl dithioacetate (0.0708 ml, 0.747 mmol) is added to 2-[4-(5(S)-aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluorophenyl]-4H-[1,3,4]thiadiazin-5-one (0.200 g, 0.617 mmol) and triethylamine (0.0946 ml, 0.679 mmol) in DMF (3 ml) and is stirred at room temperature overnight. The reaction mixture is evaporated to dryness and the residue is purified by PTLC (10% MeOH/DCM) to give a white solid (0.21 g, 90%); 1HNMR (300 MHz, DMSO-d6) δ 2.43 (s, 3H), 3.59 (s, 2H), overlapping 3.84 (dd, J=6.6, 9.1, 2H) and 3.92 (t, J=4.7 Hz, 2H), 4.19 (t, J=9.1 Hz, 1H), 4.92-5.05 (m, 1H), 7.43 (dd, J=2.2, 8.5 Hz, 1H), 7.58 (dd, J=2.2, 14, 1H), 7.69 (t, J=8.5, 1H), 10.4 (t, J=5.8 Hz, 1H), 11.6 (s, 1H); mp 182-3; MS (m/z): [M+H]+=383.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. customthe residue is purified by PTLC (10% MeOH/DCM)

Sources & evidence

ORD record
ord-d20a6a54b2c648b1b89fb486ac26fa2d
Source dataset
uspto-grants-2004_12
Patent number
US06828317B2

Reaction notes

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